Andrewsa-(0-Alkenylary1)diazoalkanes. generated from tosylhydrazone salts, cyclise to 1 H-2.3-benzodiazepines in high yield. These products isomerise to the 5H-isomers under basic conditions. The energy barriers to ring inversion for both isomers have been estimated from n.m.r. spectroscopic data.
Bromoallenes give allenic carbenes under basic conditions, which react with methylindoles to give alkenylquinolines by ring expansion and alkynyl-and allenyl-3H-indoles. Under the same conditions 2.5-dimethylpyrrole is converted into a 3-al kenyl-2,6-dimethylpyridine.
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